Contents
Introduction ............................................3 Product Profiles.......................................4 Ethylenediamine (EDA).........................4 Diethylenetriamine (DETA) ..................4 Triethylenetetramine (TETA) ................4 Tetraethylenepentamine (TEPA) ..........4 Heavy Polyamine (HPA) ........................5 Piperazine (PIP)......................................5 Aminoethylpiperazine (AEP) ................5 Aminoethylethanolamine (AEEA) ........5 Typical Physical Properties ....................6 Ethyleneamines Vapor Pressure vs. Temperature ........8 Viscosity vs. Temperature...................9 Specific Gravity vs. Temperature .....10 Ethylenediamine Aqueous Solutions Freezing Point vs. Composition.......11 Vapor-Liquid Equilibria at 760 mm Hg ................................12 Heat of Solution at 22°C ...................13 Specific Gravity vs. Temperature .....14 Piperazine Aqueous Solutions Freezing Point vs. Composition.......15 Vapor-Liquid Equilibria at 760 mm Hg ................................16 Reactions of Ethyleneamines...............17 Reaction Notes ......................................18 Ethyleneamines Applications ..............20 Major End-Uses....................................21 Lubricant and Fuel Additives..............22 Polyamide Resins .................................23 Asphalt Additives and Emulsifiers.......24 Petroleum Production and Refining....24 Resins and Additives for Pulp and Paper .....................................25 Epoxy Curing Agents............................26 Bleach Activators..................................26 Chelates and Chelating Agents...........27 Metal Ore Processing ...........................27 Surfactants and Emulsifiers ................28 Anthelmintics (Dewormers) ...............28 Fabric Softeners....................................29 Fungicides.............................................30 Textiles...................................................31 Polymers and Elastomers....................31 Other Applications ...............................31 Shipping Data........................................32 Product Specifications..........................32 Product Availability...............................33 Storage and Handling ...........................34 Health Effects ........................................35 Ecological Fate and Effects...................36 Product Safety .......................................37 FDA Status .............................................38 References .............................................40 Emergency Service................................47

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Introduction
he Dow Chemical Company, pioneered ethyleneamines development in 1935, when the company was the first to commercialize production, and has been the acknowledged world leader in the business ever since. Today, Dow manufactures ethyleneamines in two world-scale facilities at its Taft, Louisiana, petrochemicals complex. We are the only producer to use both the ethylene dichloride and reductive amination catalytic processes, thus providing unparalleled flexibility in meeting customer needs. Unexcelled quality – in product, technology, and services – is the byword of Dow’s ethyleneamines business. Another first for the company was receipt of ISO 9002 registration in 1990 for the Taft quality systems. Since then, registrations have been received for raw material quality systems, including those for ethylene, ethylene oxide, and ethanolamines, as well as for domestic and international distribution systems. In 1994, our ethyleneamines business won the Shingo Prize for Excellence in Manufacturing. The award recognizes outstanding achievements in manufacturing processes, quality enhancement, productivity improvement, and customer satisfaction. Helping to drive these evergreen quality programs is Dow’s technology leadership. Dedicated research and development focused on the ethyleneamines production processes has constantly improved product quality. Manufacturing technicians employ advanced statistical process control and zone charting for continuous improvement and reduced variability. Backing them is the in-plant laboratory with dedicated equipment for each of the ethyleneamines covered in this publication. And our applications scientists, unsurpassed in their knowledge of ethyl-eneamine end uses, are always ready to assist customers with their needs. Dow’s worldwide distribution network assures you of a readily available source of ethyleneamines.

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Product Profiles
Ethylenediamine (EDA) (1,2-diaminoethane) is the lowest molecular weight
member of the ethyleneamines family. It contains two primary amine groups and forms a maximum boiling azeotrope with water. H2NCH2CH2NH2 EDA is used primarily as an intermediate in the production of bleach activators, fungicides, chelating agents, plastic lubricants, textile resins, polyamides, and fuel additives.

Diethylenetriamine (DETA) is the second linear member of the ethyleneamines
family. It contains two primary and one secondary amine groups. Compared to ethylenediamine, DETA exhibits a broad liquid range: 207°C (405°F) boiling point at 760 mm Hg and -39°C (-38°F) freezing point. H2NCH2CH2NHCH2CH2NH2 DETA is used primarily as an intermediate to manufacture wet-strength paper resins, chelating agents, ion exchange resins, ore processing aids, textile softeners, fuel additives, and corrosion inhibitors.

Triethylenetetramine (TETA) is a liquid containing linear, branched, and cyclic
molecules. The principal tetramine structures are: H2NC2H4NHC2H4NHC2H4NH2 (H2NC2H4)3N HN NC2H4NHC2H4NH2 H2NC2H4N NC2H4NH2 Linear TETA Tris-aminoethylamine (TAEA) Piperazinoethylethylenediamine (PEEDA) Diaminoethylpiperazine (DAEP) (Bis-aminoethylpiperazine)

The major applications of TETA include epoxy curing agents, and the production of polyamides and oil and fuel additives.

Tetraethylenepentamine (TEPA) is a mixture containing linear, branched, and cyclic molecules. The structures of the major TEPA components are:
H2NC2H4NHC2H4NHC2H4NHC2H4NH2 H2NC2H4NHC2H4N(C2H4NH2)2 H2NC2H4NHC2H4N NC2H4NH2 HN NC2H4NHC2H4NHC2H4NH2 Linear TEPA Aminoethyltris-aminoethylamine (AE-TAEA) Aminoethyldiaminoethylpiperazine (AE-DAEP) Aminoethylpiperazinoethylethylenediamine (AE-PEEDA)

Among the major end-uses for TEPA are the preparation of oil and fuel additives, reactive polyamides, epoxy curing agents, and corrosion inhibitors.

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The structures of the principal components contain six or more nitrogen atoms per molecule. The primary and secondary amine groups. epoxy curing agents. and cyclic ethyleneamines. the structures of which can be deduced from the chemistry of manufacture and a knowledge of the structures present in TETA and TEPA. In addition. Piperazine (PIP) is the simplest cyclic member of the ethyleneamines family. Note: “mlm” or “mlm” = –CH 2 CH 2 – 5 .Heavy Polyamine (HPA) is a complex mixture of linear. and one tertiary nitrogen atom. AEP has a broad liquid range: boiling point of 222°C (432°F) at 760 mm Hg and a freezing point of -17°C (1. pharmaceutical preparations. The major end-use applications for HPA include oil and fuel additives. and asphalt additives. HN NC2H4NH2 Major end-uses for AEP include the production of urethane catalysts. fuel additives. an anhydrous piperazine is available in flake form. The product has two secondary amine groups.4 °F). HN NH Among the major applications for PIP are anthelmintics. corrosion inhibitors. one secondary. Aminoethylethanolamine (AEEA) is an organic base with unique properties that make it an invaluable intermediate. chelates. together with the hydroxyl group. branched. fabric softeners. Aminoethylpiperazine (AEP) is unique among the ethyleneamines: it contains one primary. and coatings. H2NC2H4NHC2H4OH Principal end-uses include surfactants. and asphalt additives. polyamides. combine the features of an ethyleneamine and an ethanolamine. commercial piperazine is often sold in aqueous solutions to facilitate handling and storage. Anhydrous PIP has a fairly high freezing point of 110°C (230°F) and a boiling point of 146°C (295°F) at 760 mm Hg. Since this narrow liquid range makes it difficult to handle. and as an intermediate for the production of triethylenediamine polyurethane catalyst.

31 x (7) (8) (9) (10) (11) (12) 0.14(3) 86.14 129.01 Electrical Conductivity at 25°C.092 49.13 Vapor pressure of the solid Extrapolated.10(7) < 0. at 25°C in Water 0.32(6) 41 110 .17 . with decomposition Solid at this condition At 42°C At 130°C Forms hydrate with time 6 .40 x 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine Molecular Weight 60.17 146.86 0.40 0.952 0.01 6. 65% Piperazine.43 x 10-4 0.72 x 10-4 (2) 0.46(6) .45(6) Vapor Pressure at 20°C.030 Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.95 x 10-4 (2) 0.32 8.39 .007 0.01 < 0.877(5) 0.4(10) — (9) 0.898 0.986 1.72 — — (9) (9) Solubility in Water at 20°C.10 103. micromhos/cm Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.15 Freezing Point.015 1.52 0.73 x 10-4 0. K1. 65% Piperazine.21 104. ˚C 11 .08 < 0.29 12.01 < 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) (2) (3) (4) (5) (6) Linear component only Typical molecular weight For Piperazine.63 10-4 10-4 7.30(1) 275(2) 86.980 0.24 0.63 x 10-4 10-4 (2) Dielectric Constant at 23°C 13.091 0.43 x 10-4 (3) 0.65 x 0. Anhydrous At 42°C/42°C At 130°C/20°C Pour point Ionization Constant.28 0.22 10.13 19.01 < 0.24(1) 189.Typical Physical Properties Apparent Specific Gravity at 20/20°C 0.24 9.35 . mm Hg 10.994 1. % by wt 100 100 100(12) 100(12) 100(12) 100(10) 14 100 100 7.036(4) 0.

heat of fusion 72. cP 1.14643 .486 (13) (14) (15) (16) At 42°C. °C 760 mm Hg 117. BTU/lb(15) 270 197 162 162 99 528 250 152 237 Heat of Combustion at 25°C.65 0.1 460.14487 .9 144 184 236 27 — (9) ∆ Boiling Point/∆p.483 1.14353 .0 242.63 0.5(10) 0.0 206.74 cal/g At 130°C.043 0.6 134.3 100.13910 .1193 1.036 0. heat of fusion 50.52 0.501 1. °C per mm Hg 0.16 26. 750-770 mm.63(14) 0.80 7.9 127.056 0.037 0.139(1) — — .1 221.64 Heat of Vaporization at 760 mm Hg.052 0. BTU/lb(16) . melting point 109.58 0.457 1.304 .058 0.045 — 0.Boiling Point.569 .12395 Heat of Formation at 25°C.9 277(8) 288(8) — 116 146.0 Refractive Index.256 .3 183 215 279(8) 54 — (9) 10 mm Hg 19.7 22.9261 .049 Absolute Viscosity at 20°C.0 83.3 161.4 140.6°C.403 .13251 . nD20°C 1.78(13) 0. BTU/lb . melting point 36°C.61 0.8 123. cal/g•°C 0.83 cal/g Estimated from vapor pressure using Clausius-Clapeyron equation Calculated from gross heat of combustion 7 .162(1) .4 88.8 50 mm Hg 47.68 0.513 — — (9) (9) Specific Heat at 20°C.505 1.14744 .73(11) 15.499 1.14696 .

˚F 0 1000 800 600 500 400 300 PIP 200 20 40 80 120 160 200 240 320 400 480 560 Vapor Pressure. Vapor Pressure vs. ˚C 8 . Temperature Temperature.Figure 1: Ethyleneamines. mm Hg 100 80 60 50 40 30 20 10 8 6 5 4 3 2 EDA 65% PIP DETA AEP AEEA TETA TEPA UHP HPA X 1 -20 0 20 40 80 120 160 240 320 Temperature.

0 EDA 1.1 -50 0 50 100 Temperature.Figure 2: Ethyleneamines. Viscosity vs. cP TETA AEP DETA 10.0 HPA X 1000.0 Viscosity.0 AEEA TEPA UHP 100.0 65% PIP PIP 0. ˚C 150 200 250 9 . Temperature 10000.

Figure 3: Ethyleneamines.10 1.80 0. Temperature 1.05 AEEA 65% PIP HPA X 1.95 EDA 0. Specific Gravity vs.90 TEPA UHP PIP 0. t˚C/20˚C 0.85 0.75 -20 20 60 100 140 180 220 260 Temperature.00 AEP TETA DETA Specific Gravity. ˚C 10 .

0˚C -55 0 10 20 30 40 50 60 70 80 90 100 Composition. ˚C -15 -25 -35 -45 Eutectic -53. Composition 15 5 Eutectic -0. Weight % Ethylenediamine 11 Composition of Monohydrate Composition of Dihydrate .Figure 4: Ethylenediamine Aqueous Solutions. Freezing Point vs.8˚C -5 Temperature.

Vapor-Liquid Equilibria at 760 mm Hg 120 Vapor Phase 116 Liquid Phase Temperature.Figure 5: Ethylenediamine Aqueous Solutions. ˚C 112 108 104 100 0 10 20 30 40 50 60 70 80 90 100 Composition. Mole % Ethylenediamine 12 .

Figure 6: Ethylenediamine Aqueous Solutions. Weight % Water 13 . cal/gm of Solution 30 25 20 15 10 5 0 0 10 20 30 40 50 60 70 80 90 100 Composition. Heat of Solution at 22˚C 50 45 40 35 -∆ Hm.

90 0.98 0. Specific Gravity vs.92 0.88 0 10 20 30 40 50 60 70 80 90 100 Composition.Figure 7: Ethylenediamine Aqueous Solutions.96 Specific Gravity at 20/20˚C 0. Weight % Ethylenediamine 14 .94 0. Temperature 1.00 0.

2˚C 20 0 Eutectic -1˚C -20 0 10 20 30 40 50 60 70 80 90 100 Composition. Composition 120 100 80 Temperature. Weight % Piperazine Studies show evidence of a metastable freezing point in the region of 20 wt.% piperazine Composition of Hexahydrate 15 . Freezing Point vs.Figure 8: Piperazine Aqueous Solutions. ˚C 60 40 Eutectic 33.

Vapor-Liquid Equilibria at 760 mm Hg 150 145 140 135 Vapor Phase 130 Temperature. ˚C 125 Liquid Phase 120 115 110 105 100 95 0 10 20 30 40 50 60 70 80 90 100 Composition. Mole % Piperazine 16 .Figure 9: Piperazine Aqueous Solutions.

Other ethyleneamines react similarly. depending upon structure.Reactions of Ethyleneamines† † Illustrated by reactions of ethylenediamine (EDA). 17 .

or acyl halides to form amidoamines and polyamides.Organic Acids Ethyleneamines react with acids. to form mixtures of hydroxyalkyl derivatives (12-14). . water soluble salts. . esters.Epoxides Ethyleneamines react readily with epoxides. RX 6. RX 4.Aziridines Aziridines react with ethyleneamines in an analogous fashion to epoxides (15-16).Reaction Notes RX 1. RX 2. RX 3.3). is made by reacting one mole of EDA with two moles of nitric acid and splitting two moles of water from the salt at elevated temperatures (1) . forming crystalline. This can be done without isolating the monoamide (4-8). . Product distribution is controlled by the amine-to-epoxide mole ratio.Alcohols and Alkylene Glycols Simple aliphatic alcohols can be used to alkylate ethyleneamines with hydrogen in the presence of a reductive amination catalyst (17).or liquid-phase reactions of ethyleneamines with glycols in the presence of several different metal oxide catalysts lead to predominantly cyclic ethyleneamine products (18). RX 5. RX 7. Ethylenedinitramine. an explosive compound.Inorganic Acids Ethyleneamines react vigorously with commonly available inorganic acids. Product distribution is controlled by the ethyleneamine-to-aziridine mole ratio. . .Ureas Ethyleneamines react with urea to form substituted ureas and ammonia (11). . Various diamides of EDA are prepared from the appropriate methyl ester or acid at moderate temperatures (2. acid anhydrides. . 18 . Monoamides can be cyclized to form imidazolines. Either gas.Nitriles Hydrogen cyanide (HCN) and aliphatic nitriles (RCN) can be used to form imidazolines (9-10).

RX 8. or nitrous acid. and oxygen. crosslinked. nitrogen oxides. Ethylene thiourea. RX 10. the reaction being mildly exothermic.Sulfur Compounds EDA reacts readily with two moles of carbon disulfide (CS2) in aqueous sodium hydroxide to form bis sodium dithiocarbamate. in concentrated aqueous solutions. reaction conditions. they are sufficiently reactive that upon exposure to adventitious water. Product distribution is controlled by reactant ratio. and structure of the ethyleneamine.Environmental Reagents: CO2. react with ethyleneamines to form various polymeric. O2 Under normal conditions ethyleneamines are considered to be thermally stable molecules. Mixing methylene chloride and EDA reportedly causes a runaway reaction (19). water-soluble cationic products or higher ethyleneamine products. H2O. metal complexation or choice of solvent. RX 9. trace levels of byproducts can form and increased color usually results. Carbon dioxide reacts readily with EDA in methanol to form crystalline N-(2-aminoethyl)carbamate (23). nitrites. . amine hydrates may form. . .or disubstituted derivatives. carbon dioxide. N-Alkyl-piperazines and piperazine can react with nitrosating agents. However. activated by electron withdrawing groups. Ethyleneamines are soluble in water. .Aldehydes Ethyleneamines react exothermically with aliphatic aldehydes. The hydrates of linear TETA and PIP melt around 50°C (25-26). However. such as nitrogen oxides. Aliphatic dihalides. depending on the reactant ratio (20). 19 . react with ethyleneamines to form mono. a suspect human carcinogen. to form nitrosamine derivatives (24). such as ethylene dichloride. is prepared by reacting CS2 in aqueous EDA (22). RX 11. which can be reacted with zinc (or manganese) to give the appropriate dithiocarbamate salt. Reactions of aldehydes with such ethyleneamines as EDA or DETA give mono. NOx. The products depend on stoichiometry.and disubstituted imidazolidines via cyclization of the intermediate Schiff base (21).Halides Alkyl halides and aryl halides.

They are predominantly used as intermediates in the production of functional products.Ethyleneamines Applications Ethyleneamines are utilized in a wide variety of applications because of their unique combination of reactivity. . basicity. The following table lists the major end-use applications for these versatile materials. and surface activity.

Major End-Uses for Ethyleneamines Application Lube Oil Additives Fuel Additives Polyamide Resins Asphalt Chemicals Corrosion Inhibitors Wet-Strength Paper Resins Epoxy Curing Agents Bleach Activators Chelating Agents Ore Flotation Agents Surfactants Fabric Softeners Fungicides Anthelmintics Spandex Fibers Urethanes Military Decontamination Agents Plastic Lubricants Ion Exchange Resins Coatings NOTE: The largest volume applications are indicated by ++ EDA DETA TETA TEPA Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine HPA PIP AEP AEEA Heavy Polyamine Piperazine Aminoethylpiperazine Aminoethylethanolamine EDA DETA + TETA + + ++ + + ++ TEPA ++ + ++ + + + ++ HPA ++ PIP AEP AEEA ++ ++ + + ++ ++ ++ + + ++ ++ + + ++ + + ++ ++ ++ + + ++ ++ ++ + + ++ + + + ++ ++ + + + ++ 21 .

and bis-polyisobutenyl-succinimides. 22 . normally prepared by the condensation reaction of polyisobutenyl-succinic anhydrides (PIBSAs) (1. The ethyleneamine derivatives most commonly employed for these tasks are the mono. Ethyleneamines are also used in dispersant- sludge and varnish deposits within internal combustion engines by inhibiting the aggregation of particles. all the ethyleneamines have been employed for various products (45).Lubricant and Fuel Additives The largest application area for ethyleneamines is in ashless dispersants for engine oils and other lubricants. by solubilizing oil-insoluble liquids. Post-treatments of the succinimides are commonly utilized for performance improvement in engine oils (4658). 2) with ethyleneamines (3-44). and by neutralizing acidic species formed in the combustion process. Besides the more common means of linking long-chain hydrophobic moieties to ethyleneamines via the succinimide linkage. They are prepared on a commercial scale by reaction of an alkylphenol with formaldehyde and an ethyleneamine (71-76). The alkyl and ethyleneamine moieties are similar to those used in the succinimide products. a different linkage is employed in another important class of ashless dispersants – the Mannich bases (60-70). The higher molecular weight ethyleneamines are most popular for these derivatives. varnish inhibitors for lubricating oils for twostroke engines (59). The lubricant additives function mainly to reduce the formation of however. and in certain dispersantdetergents for fuels.

and as corrosion inhibitors in alkyd paints (7). 4). abrasionresistant. EDA. DETA. film. They are also used in preparing fatty acid/amine soaps and poly(urea) thickeners for lubricating greases. Anti-rust additives for lubricating oils have also been prepared by reacting ethyleneamines with fatty acids followed by reaction with polyalkylenesuccinic anhydrides (77. Cetane improvement in diesel fuels has been reported for a mixture containing EDA (96). to plasticize nitrocellulose lacquers (6). These polyamides are used in hot-melt. Dispersant-detergent additives useful in gasoline are prepared by the direct alkylation of ethyleneamines with chlorinated polybutenes (81-86). for example. PIP and certain PIP derivatives are used with EDA in certain cases (3. Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper. 78). They are also used to modify alkyd resins in certain thixotropic coating systems (5). Being soluble in alcohol-based solvents and exhibiting outstanding adhesion to polyolefins. and foil webs (8).and tetramines are sometimes used at low levels to achieve specific performance (2). they are particularly suited to these applications. via chlorination. overprint varnishes.and polybasic fatty acids. Numerous similar products made generally by alkylating or acylating EDA or DETA (87-95) are also used as fuel detergent and deposit control additives. and AEEA have found significant commercial application as dispersant detergent additives for gasoline when made by this route. pressure-sensitive. Polyamide Resins The main polyamide resin type. Oil additives providing detergent properties have also been prepared from ethyleneamines (79. to provide a reaction site. in addition to the liquid resins used as epoxy hardeners. cellophane. paper. a number of antiwear/antiscuff additives for lube oils and greases also use ethyleneamines. 80). Thermoplastic polyamides are similarly used in formulating glossy. These additives are prepared from ethyleneamines by reaction with various viscosity index improvement polymers that have been modified. plastic. 23 . and. and heat-seal adhesives for leather. is that prepared generally by the condensation reaction of diamines with di. and paper. and metal.Lubricant and Fuel Additives (cont’d) Additives for lubricating oils providing a combination of viscosity index improvement (VII) and dispersancy have also been reported. polyester. however. tri. EDA is a principal amine reactant (1).

. They are usually applied to the petroleum well by any of several methods designed to create a film of inhibitor on the surfaces of the steel structures in the petroleum well. and in the processing of certain catalysts (22-25). 13). patching. Corrosion inhibitor formulations for downhole petroleum production applications use a significant volume of ethyleneamines. Similar ethyleneamine derivatives are used to make stable asphalt-in-water emulsions (8-16). ethyleneamines can be used to decrease the migration of injected chemicals into the formation by adsorption and precipitation (14). TEPA and other ethyleneamines combined with thickeners help stabilize viscosity. 11. and their mixtures are used in antistrip formulations and asphalt-in-water emulsions. These are generally used as their HCl or acetic acid salts. 12. to separate alkenes from thermally-cracked petroleum products (20). they are represented by the products made from DETA and fatty acids (1-7). to separate carbon disulfide from a pyrolysis fraction (21). and TETA. and polyamides. mobility. They generally utilize the condensation reaction products of higher ethyleneamines and fatty or dimer acids.and bis-amidoamines. Specific ethyleneamine derivatives can also be used for water clarification (16.e. The oil-water emulsions generated at times by petroleum wells can often be broken with certain ethyleneamine derivatives (8-10) (EDA. Typically. as part of a system used to extract thiols from petroleum distillates (18).Asphalt Additives and Emulsifiers Mono. imidazolines. These films displace the corrosive production fluids and attract a film of petroleum which further isolates the steel from the fluid. Ethyleneamines are also employed in petroleum refining operations. mono. DETA. i.and bis-amidoamines. neutralizers. They are typically prepared from the higher molecular weight ethyleneamines and fatty acids (1-7). imidazolines. and pH and increase resistance to hydrolysis (15). Antistrip additives promote adhesion between the mineral aggregate and the asphalt in mixtures for road paving. demulsifiers. 24 . 17). for example. as part of a composition used as an antioxidant to control fouling (19). and surfacing. and functional additives. Petroleum Production and Refining A number of ethyleneamine derivatives are also employed in petroleum production and refining operations as corrosion inhibitors. In some secondary recovery operations.

both urea. 25 . 27). The bis-amide made by reacting EDA with stearic acid. are also used. adipic acid and epichlorohydrin (37). rather than the Certain pigment retention and drainage additives made with ethyleneamines include various polyamides (10. The sulfur-free delignification of wood chips with EDA-soda liquors has received some interest in the past few years (22-24). waterproofing and sizing compounds (14-16). The cationic formaldehyde resins. 8). TETA. Numerous modifications of this resin type have been reported (4. added to the beater stock to improve the wet strength of tissue. 11) and polyamines (12). and polyamine resins. The most popular paper wet strength resins are the modified polyamides typically made with DETA. Ethyleneamines are also used in the preparation of certain flocculating agents (13).Resins and Additives for Pulp and Paper Ethyleneamine-based chemicals are used widely in the paper industry to impart specific functional characteristics to the finished paper. and/or TEPA in the resin backbone to provide substantivity to the cellulose fibers in paper. 2). toweling. 6. Polyamine wetstrength resins. incorporate ethyleneamines such as DETA. polyamide. and acidic conditions required by modified formaldehyde resins. these types of paper wetstrength resins have been decreasing in popularity due to the adverse health effects associated with formaldehyde. packaging paper products. Even though they tend to be less expensive. These resins can be used under less corrosive neutral or alkaline conditions. is used as a defoamer in paper mill operations. made by the reaction of ethyleneamines with epichlorohydrin (9). represent a major end use for ethyleneamines. to make nonacidic papers. and paper coatings (21). Cationic formaldehyde.and melamine-formaldehyde types (1. ethylenebis(stearamide). Improved rates of EDA recovery (25) have also been developed for EDA-sulfide pulping processes (26. antistatic agents (17-20).

(1). such as ethylene oxide. Although the ethyleneamines themselves are often used as the curing agent or part of a curing agent package. etc. Mannich bases prepared from a phenol.Epoxy Curing Agents All the commercial ethyleneamines are used either neat or as derivatives for curing epoxy resin-based coatings. adhesion. made by the reaction of EDA with acetone. patibility with liquid epoxy resins (9-13). handling. which is then reacted with two moles of acetic anhydride to form the tetra-amide. a common modification is the addition of an alkylene oxide. It is prepared by first reacting EDA with two moles of acetic acid to form the bis-amide. are widely used for longer pot life and better flexibility. they are commonly modified in various ways to achieve performance. to DETA (2) as shown above. formaldehyde. adhesives. Most of the amidoamines and reactive polyamides contain significant levels of imidazoline structure. and tertiary amino functionality to catalyze that reaction. and a variety of other ethyleneamine modifications (15-18). and safety improveAmidoamines and reactive polyamides prepared by condensation of TETA or higher polyamines with fatty acids (3-5) and dimer acids (6. respectively. 7). For example. castings. and solvent resistance (8). grouts. ketimines. cyanoethylation. The presence of different polyamino functionalities in the higher ethyleneamines allows partial reaction with various modifiers while retaining sufficient primary and secondary amino functionality for reaction with the epoxy resin portion of the system. Other modifications of the ethyleneamines include partial reaction with epoxy resin to form a prepolymer. Bleach Activators Tetraacetylethylenediamine (TAED) has been widely adopted for use in home laundry products as an activator for peroxygen bleaches. to give derivatives providing longer pot life and better wetting of glass (14). which provides improved com- ments. and a polyamine. 26 . usually by reaction with acrylonitrile. laminates.

or separated and hydrolyzed separately (4. 27 . 5). AEEA and DETA are also used to make similar polyacetic acid or acetate products. and the ethyleneamines themselves aid extraction of copper. called chelates. 2). 2). has found application recently in chlorine-free paper pulp bleaching to prevent iron from decreasing efficiency of the hydrogen peroxide (6). Diethylenetriaminepentaacetate (DETPA). where their metal complexing properties are required. or need to be buffered. and as ingredients in systems for etching and for stripping nickel and nickel alloy coatings.or polyvalent metals. This property makes the ethyleneamines useful in specialized applications. Chelating resins. and formaldehyde in the presence of sodium hydroxide (1. They operate by forming stoichiometric complexes. such as zinc and copper. chromium. and in lead ore processing and recovery operations (5-8). These same kinds of derivatives can be used for beneficiation of niobium and tantalum ores (3). concentrated. 8). separated. These derivatives selectively adhere to silica particles and permit their removal by flotation procedures (1. made from DETA. The intermediate polynitrile may either be hydrolyzed in situ (3).Chelates and Chelating Agents Polycarboxylic acids and their salts derived from ethyleneamines are used in a variety of applications where specific metal ions interfere with processing. They may be made also by reaction of the ethyleneamine with sodium chloroacetate. These compounds are produced on an industrial scale primarily through the reaction of the ethyleneamine. such as electroplating and electroless metal coating with specific metals and many alloys. made from EDA. or transported. sodium or hydrogen cyanide. and nickel from their sulfide and oxide ores (4). with most di. and fibers (9) have also been developed. The most important commercial family of chelating agents is ethylenediamine tetraacetic acid (EDTA) and its various sodium salts. polymers (7. It should be pointed out that unmodified ethyleneamines also form stable complexes with certain metal ions. Metal Ore Processing Certain processes for enrichment of iron and phosphate ores use amidoamines and imidazolines made from ethyleneamines and fatty acids.

and the imidazoline formed by the reaction under vacuum at virtue of their mildness and good foaming characteristics. A variety of 2-alkylimidazolines and their salts prepared mainly from EDA or AEEA are reported to have good foaming properties (3-8). elevated temperature to remove two moles of water are all used. AEEA-based imidazolines are also important intermediates for surfactants used in shampoos by TETA. amine salts or soaps obtained by simply mixing the amine with a fatty acid (1. The PIP salts have long been the agents of choice for use against roundworms and pinworms (1). Anthelmintics (Dewormers) Piperazine is the active ingredient in certain veterinary anthelmintic preparations – primarily for combating intestinal worms in poultry and swine. or TEPA and fatty acids also function as water-in-oil or oil-in-water emulsifiers (12). TEPA. ethoxylated with an average of 17 moles of ethylene oxide. improves the soil antiredeposition and clay soil removal properties of certain liquid laundry detergents (13). The imidazolines are generally converted into amphoteric surfactants for this application by reaction with one or two moles of sodium chloroacetate (9-11).Surfactants and Emulsifiers To prepare surfactants derived from ethyleneamines. amidoamines derived by the non-cyclicizing reaction between amine and acid. 2). 28 . The products of a reaction between DETA.

Softeners based on bis-imidazoline compounds are also prepared by condensing TETA or TEPA with fatty acids (7) or triglycerides (8). made from DETA and fatty acids. such as AEEA. they have gained some popularity where environmental biodegradation concerns outweigh their The most common ethyleneamine-based fabric softeners are bis-amidoamines. to yield compounds that can be formulated into softener products for home laundry use (4-6). 2). followed by quaternization with dimethyl sulfate.Fabric Softeners Softeners are commonly added to textile materials to make them less harsh. are more subject to hydrolysis than the amidoamine and imidazoline compounds. that are either cyclized to the corresponding imidazoline by further dehydration. Softeners are added to the home washing machine during a rinse cycle or as part of a detergent/softener combination product. or sodium chloroacetate. The amino esters. “softer” or more pleasing to the touch. 29 . and impart fluffiness. generally with dimethyl sulfate. These intermediates are then quaternized. decreased storage stability and performance. As a result. Amino esters are made from acids and an amino alcohol. Softening agents based on DETA and TEPA are also used in industrial textile processing operations (1. or to the clothes dryer. as well as their quaternized derivatives. Softeners also act as antistatic and antisoiling agents. or reacted with ethylene oxide (3) to convert the central secondary amine group to a tertiary amine. which gives amphoteric softeners (9).

vegetable. The ammonium (amobam) and mixed zinc and manganese (mancozeb) salts are also known. However. prepared from EDA and stearic acid. Other materials based on EDA have also been suggested as fungicides. The EBDCs are prepared by reacting EDA with carbon disulfide in the presence of an aqueous base. preventative. potato. 30 . Zineb and maneb are normally formed by the addition of zinc or manganese salts to nabam solutions. was found to be unstable. A 2:1 EDA-copper sulfate complex has been suggested for control of aquatic fungi (10). rust. It is used as the acetate salt for control of apple scab and cherry leaf spot. They are used on many fruit. scab. The zinc (zineb) and manganese salts (maneb) are especially effective (1-7) and are today the azoline (9). primary commercial products.Fungicides The ethylenebisdithiocarbamates (EBDCs) are a class of broad-spectrum. nabam. and blight. and grain crops for prevention of mildew. contact fungicides first used in the early 1940’s. it is stabilized by conversion to certain other divalent metal salts. The most important of the imidazoline type (8) is 2-heptadecyl-2-imidS CH2–NH–C–S–Na H2C–CH2–CH2–NH2 + CS2 + 2NaOH CH2–NH–C–S–Na S + 2 H2O This sodium derivative.

plaster systems. explosives. TETA has been recommended as a curing agent for furfural resin binders in foundry molds and molded graphite. 2). Acrylate and other monomer vapors can be efficiently removed from vent streams with scrubber solvents containing TETA. catalysts (TEDA [triethylenediamine] is a significant example). ceramics. static prevention (6). 31 . gas and water treating. pharmaceuticals. light stabilization of spandex fibers (4). petroleum production. industrial corrosion inhibition. as precursors for certain compounds providing durable press (3). The bisamidoamine condensate made from TETA or TEPA and stearic acid is used as a defoamer in certain textile treatment baths. and for etching polyimide films. viscosity regulator. functional fluids. preservative. and as a parting material. fire retardants. TETA. in phenolic resin curing. including the treatment of a wide variety of natural and synthetic fibers for modification of certain properties (1. to reduce static in polystyrene foam. and TEPA (8-10). Urethane systems and processes employ certain ethyleneamines and their derivatives as curing agents. They include coal-oil emulsification and coal extraction. Polymers and Elastomers EDA is a key component of the polymer in spandex fiber. EDA reacted with stearic acid makes ethylene-bis(stearamide) (EBS) that is used as an external lubricant for ABS resin and PVC. and membranes. EDA is used in preparing silane and silanol compounds that improve the adhesion between inorganic surfaces and polymer films. ion exchange resins. EDA specifically can be used as a stabilizer for certain urea resins. Dye assist compounds for synthetic fibers have been derived from EDA. and polyol starters. to inhibit isoprene polymerization. Ethyleneamines find application in vulcanization processes for certain rubbers (1-11). and mothproofing (7). and they are used in styrene-butadiene latex processes to coagulate the low levels of finely-dispersed particles in the reaction medium (12-15). polymer concrete and concrete additives. shrinkproofing wool (5). DETA is a component of Nylon 6 (11). Other Applications Ethyleneamines find application in numerous other specific industries. stone and concrete coatings. DETA. and surface gloss enhancer.Textiles Ethyleneamines are used in the textile-related industries for a variety of applications.

011 1.57 (5) At 80 °C at 15.Shipping Data Since governmental regulations are subject to change. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 0.24 8. 65% Piperazine. kg Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.949 0.015 — (2) — (2) 0. 65% Piperazine. labeling and container requirements may be obtained by contacting Dow at the numbers on the back of this booklet.896 0.977 0. 32 .56°C 0.60 Metric Units Average Weight per liter.031 Product Specifications Product specifications and methods are available upon request.95 8.980 0. We will provide a technical contact to discuss specific questions you might have.991 1.56°C 7. Average Weight per gallon.44 8.39 (1) — (2) 8.92 8. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 7.027 (5) At 80 °C at 15.953 0.51 7.15 8.18 8. additional information on shipping data.30 8.27 8.21 8.005 (1) — (2) 0.900 0.987 1.984 1.48 7.47 — (2) — (2) 8. Please contact Dow at the numbers on the back of this booklet. lb Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.995 1.

ASTM Method D 56 P = Pensky-Martens Closed Cup.000769 (3) 0.00086 0.00794 0.00092 0. per °C at 20°C 0.00110 0.00106 0.00095 (5) — (2) 0.00085 0.00089 0.00642 (3) 0.00076 — (2) — (2) 0.00703 0. ASTM Method D 93 C = Cleveland Open Cup.000767 (3) Coefficient of Expansion. 33 .00081 0.000792 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00081 0.00661 0. per °C at 20°C 0. ASTM Method D 1310 ∆kg/liter/∆t 10°C to 30°C.00080 0.00077 at 55°C 0.00106 0. per °C 0. °F Closed Cup 110 T 208 P 300 P 340 P 345 P None T 130 P 215 P 260 P Open Cup 103 TO 225 C 310 C 360 C 445 C 205 C 215 C 250 C 310 C (6) T = Tag Closed Cup. ASTM Method D 92 TO = Tag Open Cup.00640 (3) Coefficient of Expansion.00076 — (2) — (2) 0. per °C 0.00089 0.00080 0.00680 (3) 0.000815 (3) 0.00092 0. rail car.∆lb/gal/∆t 10°C to 30°C.00083 0.00077 Flash Point (6). ASTM Method D 93 C = Cleveland Open Cup.00077 Flash Point (6).00081 0.00083 0. tank truck.00076 0. ASTM Method D 92 TO = Tag Open Cup.000747 (3) 0.00095 (5) — (2) 0.00077 at 55°C 0.00110 0.000842 0. and nominal 55gallon drums.000951 0. ASTM Method D 1310 Product Availability Products are available in bulk ocean tanker.00076 0.000943 (4) — (2) 0.00086 0.00085 0.00787 (4) — (2) 0. °C Closed Cup 43 T 98 P 149 P 171 P 174 P None T 54 P 102 P 127 P Open Cup 39 TO 107 C 154 C 182 C 229 C 96 C 102 C 121 C 154 C (6) T = Tag Closed Cup.00623 (3) 0.00081 0.

and either smoldering or a flame may be observed. for nonaqueous. If this cannot be tolerated. any of these media contaminated with ethyleneamines should be washed with water to remove the amines. In some cases. Nonmetallic equipment is not normally used for ethyleneamine service. 34 . No single elastomer is acceptable for the entire product line. This may lead to low levels of byproducts and increase the color of the product. Carbon steel is not recommended for EDA. consistent with local and federal regulations. this may lead to spontaneous combustion. but the products will pick up iron and discolor badly. certain grades of these materials may be acceptable in some storage applications. and small agitated tanks. Risk of insulation fires can be reduced by insisting on good housekeeping.g. copper and copper-bearing alloys are unacceptable for all ethyleneamine service. like many other combustible liquids. maintenance of weather barriers. dedicated processing equipment is recommended. or AEEA storage tanks. However. Ethyleneamines can permeate polyethylene and polypropylene. However. even at ambient temperature. dumped filter cake. TFE is an alternative to elastomers since it is resistant to ethyleneamines. valves. Modest storage temperature (less than 60°C) and nitrogen blankets will allow the use of carbon steel. self-heating of ethyleneamines may occur by slow oxidation in other absorbent or high-surface-area media. However. Consequently. Most commonly used industrial thermal insulating materials are acceptable for ethyleneamine service. nitrogen oxides. since TFE is not a true elastomer. heating coils. Also.Storage and Handling Ethyleneamines react with many other chemicals. except EDA. DETA. and training personnel. in dedicated service. Water.001 in/yr) at typical storage temperatures. minimizing insulated flanges and fittings. inert atmosphere (such as low CO2-containing nitrogen) will minimize this sort of degradation. A 300 series stainless steel is often specified for pumps. e. Galvanized steel. Closed cellular glass insulation is normally resistant to insulation fires because it is difficult for the ethyleneamines to saturate these materials and also difficult for air to contact the product.. sometimes rapidly and usually exothermically. Recommended gaskets for ethyleneamine service are made of GRAFOIL™ flexible graphite or polytetrafluoroethylene (TFE). carbon dioxide. or be thoroughly wetted with water and then disposed of in closed. porous insulation may introduce the hazard of spontaneous combustion if the insulation is saturated with ethyleneamines from a leak or external spill. heavier ethyleneamines without noticeable impact on product quality. spill absorbents and metal wire mesh (such as that used in vapor mist eliminators). then 300 series stainless steels are recommended for the storage tanks. Carbon steel with baked phenolic lining is acceptable for storage of many pure ethyleneamines. Proper selection of materials of construction for ethyleneamine service is essential to ensure the integrity of the handling system and to maintain product quality. To avoid this situation. Storage under a dry. Carbon steel transfer lines or agitated equipment will suffer enhanced corrosion because of erosion of the passive film by the product velocity. watersaturated containers. and oxygen from the atmosphere may be absorbed by the amines. transfer lines. Corrosion is not extreme (<0. it may not always prove suitable as a replacement material.

solid amine hydrates may form. vent lines and safety devices. contact Dow at the numbers on the back of this booklet and request our Ethyleneamines Storage and Handling Brochure and/or a technical contact who will discuss specific questions about acceptable materials of construction and storage practices. For additional information. which can be a nuisance in handling. contaminants can lower the onset of rapid exothermic thermal decomposition (for example. This information is of a general nature. ethyleneamines exhibit good temperature stability. Vent units require periodic inspection to verify that fouling is not occurring and to ensure that seals are functioning properly to exclude air from the tank. Warm water cleanup can reduce the extent of the problem. Additionally. as well as recommended safety procedures. may be found in the Material Safety Data Sheets. vent units and relief devices may be steam-traced to maintain 160°C. although the amines are water-soluble. Hydrate problems are usually avoided by insulating and heat tracing equipment to maintain a temperature of at least 50°C. Additionally. Also.The amines do not present any unusual flammability problem at ordinary temperatures. As commercially pure materials. EDA has the lowest flash point (Tag Closed Cup): 43°C (110°F). mineral acids contamination). Tank vents and safety devices are also susceptible to fouling by solid amine carbamates formed by the reaction of the amines with carbon dioxide. Water cleanup of ethyleneamine equipment can result in hydrate problems. This degradation increases in rate as the temperature and/or time increases. Storage at elevated temperatures can cause vapors “breathing” from the tank to contain significant concentrations of product. contact Dow at the numbers on the back of this booklet. heavier ethyleneamines may be stored at elevated temperatures (40-60°C) to ease inplant handling by lowering the viscosity. Health Effects Information on health effects and their management. Vent fouling can be reduced by using nitrogen blankets on storage tanks to exclude atmospheric CO2. Testing for thermal stability is suggested whenever ethyleneamines are mixed with other materials. which causes the carbamates to decompose. in certain concentrations. even in areas where routine processing is nonaqueous. Ethyleneamines are typically maintained above their freezing points which may require storage above ambient temperatures (particularly EDA and PIP). All amine vents should be routed to a safe location and “smoking vents” routed to water scrubbers to capture the vapors. In addition. which are updated as new information becomes available. For the latest Material Safety Data Sheets on ethyleneamines. 35 . Hydrates can plug processing equipment. At elevated temperatures some product breakdown may be observed in the form of ammonia and the formation of lower and higher molecular weight species.

54 Nitrogenous Calc.68 1. (ThOD) mg/mg(1) Product Evaluated Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. 65% Aminoethylpiperazine Aminoethylethanolamine Carbonaceous Meas.50 1.49 1. (1989). while the nitrogen converts to and remains as ammonia. 10. which rapidly biodegraded. Nonacclimated domestic sewage microorganisms used as seed. 17th ed.94 1.63 Calc. Bacterial inhibition tests indicate that none of these amines tested should be inhibitory to conventional wastewater treatment processes at expected discharge levels of less than 500 mg/L.64 1. The biooxidation values are calculated as percentage ratio of BOD and ThOD (BOD/ThOD x 100).55 1..48 1. DETA. except for EDA and AEEA. and Standard Methods techniques.Ecological Fate and Effects Dow has conducted a series of laboratory studies on the biodegradation and ecological effects of these amines. TETA. Natural acclimation in a wastewater treatment plant or in the general environment would be expected to increase the rate and extent of biodegradation for the related compounds.13 1. with the exception of EDA/DETA studies which used acclimated seed. Biodegradation was measured by the riversimulating 20-day biochemical oxygen demand (BOD) test using nonacclimated microorganisms. (3) The measured biooxidation as a percent of the total carbonaceous and nitrogenous oxygen demand (sum of calculated carbonaceous and nitrogenous ThOD values) is presented for Days 5.28 1. showed more toxicity to Daphnia magna with LC50 values ranging from 5 to 40 mg/L. The nitrogenous oxygen demand is calculated based on nitrogen being oxidized to nitrate by nitrifying bacteria. Several amines. 1. 36 .93 1.75 — — 1.86 1. Ecological Fate and Effects of Ethyleneamines Theoretical Oxygen Demand. and AEP.84 1. Aquatic toxicity measurements showed only moderate toxicity for most of the tested amines.23 (1) Measured by Chemical Oxygen Demand (COD) procedure published in Standard Methods for the Examination of Water and Wastewater. (2) Measured in dilution bottle biochemical oxygen demand test published in Standard Methods. ASTM. Public Health Assoc. (COD) 1.33 1.86 1. EDA.88 1. 2. Calculated value based on oxygen required to oxidize the chemical to carbon dioxide and water. The impact of acclimation on the rate and extent of biodegradation is shown by the EDA and DETA acclimated seed data.86 1. These studies were conducted by procedures which follow the EPA. The data presented in the following table show that the amines biodegrade slowly.69 — 1. and 20.

you should review our latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely. contractors. it is the user’s responsibility to determine that this information is appropriate and suitable under current. Before handling any other products mentioned in the text. For Material Safety Data Sheets and other product safety information.Product Safety When considering the use of any Dow products in a particular application. medical device. or any other users of the product(s). mg/L 48-hour 96-hour Daphnia magna Fathead Minnow 5 (4-6) 17 (15-19) 40 (35-50) — — 90 (80-110) 36 (25-50) 110 (90-130) 210 (190-230) 260 (220-310) 330 (280-400) 310 — 720 (640-800) 560 (500-620) 515 (470-560) (4) Determined by turbidity/growth procedures where the median inhibition concentration (IC50) is measured after 16 hours of incubation with sewage microorganisms. you should obtain available product safety information and take necessary steps to ensure safety of use. The customer should furnish the information in these publications to its employees. applicable laws and regulations. understand. mg/L Aquatic Toxicity (5) LC50. Dow requests that the customer read. No chemical should be used as or in a food. 37 . or cosmetic. Biochemical Oxygen Demand(2). drug. (6) Biooxidation values for EDA and DETA are taken from tests with acclimated microorganisms. and customers. medical device. or cosmetic until the user has determined the suitability and legality of the use. Since government regulations and use conditions are subject to change. No nitrification was measured in the acclimated systems. drug. or in a product or process in which it may contact a food. (5) Fathead minnows and Daphnia magna bioassays were conducted using procedures published by EPA and ASTM. The 95% confidence limits (95% CL) are shown in parentheses. and request that t hey do the same. and comply with the information contained in this publication and the current Material Safety Data Sheet(s). % biooxidation Total Carbonaceous(2) Days 5/10/20 68/100/100 A36(6)/A45(6)/A70(6) <5/<5/<5 A23(6)/A46(6)/A70(6) 3/4/9 4/7/12 <5/<5/<5 <10/<10/<10 2/4/7 2/64/90 —/—/— —/—/— —/—/— —/—/— —/—/— —/—/— 1/37/53 >5000 680 — — 4600 1400 >5000 25/37/78 1000 Nitrogenous(3) Days 5/10/20 Bacterial (4) Inhibition IC50. contact Dow at the numbers on the back of this booklet.

applied to the sugar mill grinding. Catalyst for epoxy resins used as the food contact surface of paper and paperboard in contact with fatty. Accelerator in vulcanization of rubber articles intended for repeated use.320 175. Modifier for urea-formaldehyde and melamine-formaldehyde resins used as the basic polymer in resinous and polymeric coatings on a metal substrate. Catalyst for epoxy resins and component of polyamides for use in zinc-silicon dioxide matrix coatings.25 173. or holding food.5 wt% of the rubber product.2600 178.300 175. it is the responsibility of the user of an ethyleneamine as a Direct or Indirect Food Additive to read and understand any applicable FDA regulations in Title 21 of the Code of FDA Regulation Ethylenediamine 21 CFR Permitted Uses 173. Catalyst activator in semirigid and rigid acrylic and modified acrylic plastics. at a level not to exceed 0.1200 177. and/or diffusor systems at a maximum level of 1. Polyamide-epichlorohydrin resins prepared by reacting adipic acid or other acids with diethylenetriamine to form a basic polyamide and further reaction of the polyamide with other materials to form water-soluble thermosetting resins for use in the manufacture of paper and paperboard.180 176. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for modifying urea-formaldehyde resins used as the basic polymer and as a resin to anchor coatings to the substrate in the manufacture of food-packaging cellophane.300 175. transporting. Modifier for urea-formaldehyde and melamine-formaldehyde resins for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with fatty.1200 177.300 175.300 177. as a modifier for melamine-formaldehyde resins used in cellophane. Modifier for melamine-formaldehyde resins for use as the basic polymer in cellophane. sulfanilic acid. Formulation of defoaming agents used in the manufacture of paper and paperboard prior to and during the sheet forming operation.0 ppm based on the weight of raw cane processed.180 176. and/or diffusor systems at a maximum level of 2. However. aqueous.170 176. not to exceed 1. crusher.105 175.4’-iso-propylidenediphenol epichlorohydrin epoxy resins. Modifier for urea-formaldehyde resins for use as the basic polymer in cellophane and as a resin to anchor coatings to substrate.180 176.5 wt% based on the monomers.180 176.FDA Status Dow provides the following FDA Status Summary for the convenience of our customers. Adjuvant in the preparation of slimicides used as antimicrobial agents to control slime in the manufacture of paper and paperboard. 175. crusher. and as a resin to anchor coatings to substrate. Catalyst for epoxy resins and component of polyamides for use in xylene-formaldehyde resins condensed with 4. aqueous. Component in an antimicrobial formulation used in cane sugar mills.390 176.180 176.1210 177. Polyamides from vegetable oil acids and sebacic acid for use in side seam and can-end cements. Modifier for amino resins used as a component of the coated and uncoated food-contact surface of paper and paperboard in contact with fatty.380 175.1200 177.20 173. Component of adhesives used in articles intended for packaging.170 176. Crosslinker with epichlorohydrin to make ion-exchange resins used in the processing of food. and dry food. aqueous. and dry food.1200 177.300 Preparation of ion-exchange membranes used in the processing of grapefruit juice. Polyamides from dimerized vegetable oils for use as adjuncts for epoxy resins.170 176.1010 177.210 176.180 176. Catalyst for epoxy resins and component of polyamides for use in making closures with sealing gaskets.3120 38 . applied to the sugar mill grinding.0 ppm based on the weight of raw cane or beets processed.320 173. Urea-formaldehyde resins chemically modified with polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food. Catalyst and crosslinking agent for epoxy resins used in resinous and polymeric coatings applied as a continuous film or enamel over a metal substrate or applied as a continuous film or enamel to any suitable substrate provided that the coating serves as a functional barrier between the food and the substrate and is intended for repeated food-contact use.105 175. Component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food (as a crosslinking agent in polymerization). Component in an antimicrobial formulation used in cane sugar and beet sugar mills.170 176. and dry food. and other listed amines. Polyamides formed by reaction with dimerized vegetable oil acids for use as components of food-packaging adhesives. Additive in the production of animal glue. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane.

it is the responsibility of the user to determine that any such use is suitable. Furthermore. and FDA-compliant. safe. Diethylenetriamine (EDA) Triethylenetetramine (DETA) ✔ ✔ Tetraethylenepentamine (TETA) ✔ Aminoethylethanolamine (TEPA) ✔ (AEEA) ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ 39 .Federal Regulations (21 CFR) to determine any limitations or restrictions on the proposed use.

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